DL-Phenylalanine, methyl ester → (R)-Methyl 2-amino-3-phenylpropanoate

HRID 1903595Notes

Reaction equation

HRID 1903595 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:5].COC(=O)[C@H](CC1C=CC=CC=1)NC(=O)[C@H](CC(=O)O)NC(OCC1C=CC=CC=1)=O>>[CH3:1][O:2][C:3](=[O:13])[C@@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:5]

Participants

3

Reactant 2

HCID 75737DL-Phenylalanine, methyl esterHCID 10159630N-(Benzyloxycarbonyl)-L-aspartyl-L-phenylalanine methyl ester

Product 1

HCID 853474(R)-Methyl 2-amino-3-phenylpropanoateYield 62.3%

Procedure

Example 17 was repeated except for using DL-phenylalanine methyl ester instead of L-phenylalanine methyl ester to obtain 756 mg of an addition compound of N-benzyloxycarbonyl-L-aspartyl L-phenylalanine methyl ester and D-phenyl alanine methyl ester (1:1) (melting point: 105° to 111° C.; yield: 62.3% based on N-benzyloxycarbonyl L-aspartic acid).

Sources & evidence

ORD record
ord-e8a91d9819584909a97169f99ec2edc6
Source dataset
uspto-grants-1984_03
Patent number
US04436925

Reaction notes

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